🕊️ Failure Leads to Freedom | Becoming Truly F.R.E.E.

Fear ends where freedom begins.

Before I started in roofing, I spent five years in logistics.

I began as the “media guy,” taking photos, editing videos, and helping tell the company’s story. Over time, my role evolved. I grew in skill, responsibility, and leadership as the business changed and the needs changed with it.

It became the longest job I’d ever held — five years. Most of my other roles had lasted two or three.

Then my wife Chelsey started working in roofing.

Through a lot of hard work, she had an incredible first year — actually exceeding what had taken me five years to reach. I was proud of her, but it made me think.

Because a career isn’t just about money.
It’s about meaning, challenge, and alignment.

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The Crossroads

By that time, I had invested years building relationships with logistics experts across the country. I enjoyed the work and had stability.

But Chelsey and I began imagining what it might look like to work together — in a new industry, for the same company, with aligned schedules and shared goals.

There were a lot of pros:
→ Serving our community directly.
→ Learning a new skill set.
→ Working side by side.

And a lot of cons:
→ Leaving a reliable salary.
→ Learning a completely new trade.
→ Navigating the husband–coworker dynamic.

Ultimately, after many long talks between Chelsey and me on our back patio, I made the leap to Project One Roofing.

The opportunity felt greater than the fear.
But that didn’t mean I wasn’t afraid.

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Facing Fear

The fear of change is real.
For months, I battled the what ifs:

“What if I don’t make as much money?”
“I’m starting from scratch.”
“There’s so much competition.”
“What if I fail and have to start over again?”

That kind of fear is paralyzing. It sounds rational, but it hides a deeper truth:
We aren’t afraid of failing, we’re afraid of what failing says about us.

But as we’ve explored in this series, failure doesn’t define you.
It refines you.

And once you’ve faced the fear, you realize what’s really on the other side isn’t danger — it’s freedom.

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Freedom Through F.R.E.E.

I’ve grown more in the past year than I could have predicted - as a sales professional, project manager, and leader.
I’ve learned more about construction and roofing faster than I thought was possible - thanks to my wife, my team, and the people who’ve shared their decades of experience with me.

If you’re in a similar place - staring down fear, comfort, or uncertainty - maybe this framework can help:

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Power Acronym 185: F.R.E.E.

Face Responsibility
It can be scary to take a stand, but its worth it. Accept all you are and all you are not, and start moving forward. Take ownership of your choices, and stop outsourcing your outcomes.

Engage
Act in the presence of fear. Don’t let yourself be chained to comfort and familiarity. Move forward even when you don’t feel ready. Let failure become feedback, your companion, your fuel.

Expand
Seek new experiences and let them shape you. Keep growing. Build relationships, seek new ones and discover new ways to contribute. Make innovation a part of your personal and professional life.

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Final Thoughts

Failure is not easy.

Its challenge does not disappear in the presence of Power Acronyms.

But I hope that, like failure, these Power Acronyms can serve as companions of successful thinking just like failure can be.

Whether the failure is far in your past, you can still feel the sting of the pain, or you're fearing what sort of failure you'd have to face if things don't go the way you'd hope, remember that failure is rarely final.

So... Be F.R.E.E.

Fail Forward and discover the next chapter of your own story.

“No man is free who is not a master of himself.” — Epictetus

This is the final post in the Failing Forward Series. Read more through the links below:

Foundational → Fuel → Fortune → Feedback → Focus → Freedom

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